Anchor path vertex to object
I got it working, finally. The comments provided above by Duarte Farrajota Ramos and Edgel3D gave me the bread crumbs I needed.



This new model contains a few parts:


Frame - Has a Limit Location constraint to keep it in place
ArmPivot - Has a Limit Location constraint to keep it in place
Arm - Has a Limit Location constraint to keep it in place, Limit Rotation to keep it from going further than the hydraulic cylinder would allow
ArmPin - Parented to Arm
ArmPin.001 - Parented to Frame
Cylinder - Has a Limit Location constraint to keep it in place, Locked Track targeted at ArmPin with To: Z and Lock: X
Ram - Has a Copy Rotation with Target: Cylinder, X, Y, and Z


Rotation of Arm causes the cylinder to track perfectly. I was able to implement this in my actual project and complete an animation that was holding me up. Huzzah!